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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 18:28:10 UTC
Update Date2023-02-21 17:23:31 UTC
HMDB IDHMDB0033713
Secondary Accession Numbers
  • HMDB33713
Metabolite Identification
Common Name2-Undecanone
Description2-Undecanone is found in cloves. 2-Undecanone is found in palm kernel oil and soya bean oil. 2-Undecanone is an important constituent of rue oil (Ruta graveolens) and found in many other essential oils. Also found in black currant buds, raspberry, black berry peach and other fruits. 2-Undecanone is used in flavourings 2-Undecanone is a ketone, also known as methyl nonyl ketone (MNK). It is soluble in ethanol, benzene, chloroform, and acetone, but its large carbon chain renders it insoluble in water. Like most methyl ketones, 2-undecanone undergoes a haloform reaction when in the presence of a base. For example, the reaction between 2-undecanone and sodium hypochlorite yields sodium decanoate, chloroform, and sodium hydroxide. 2-Undecanone, also known as methyl nonyl ketone and IBI-246, is an oily organic liquid manufactured synthetically, but which can also be extracted from oil of rue. It is found naturally in bananas, cloves, ginger, guava, strawberries, and wild-grown tomatoes. 2-Undecanone is used in the perfumery and flavoring industries, but because of its strong odor it is primarily used as an insect repellent or animal repellent. Typically, 1 2% concentrations of 2-undecanone are found in dog and cat repellents in the form of a liquid, aerosol spray, or gel.
Structure
Data?1677000211
Synonyms
ValueSource
2-HendecanoneChEBI
Methyl nonyl ketoneChEBI
Rue ketoneChEBI
Undecan-2-oneKegg
BioUDMeSH
2-OxoundecaneHMDB
EnodylHMDB
FEMA 3093HMDB
Ketone, methyl nonylHMDB
LuparoneHMDB
Methyl N-nonyl ketoneHMDB
Methyl-N-nonylketoneHMDB
MethylnonylketoneHMDB
MGK Dog AMP MNKHMDB
Nonyl methyl ketoneHMDB
UndecanoneHMDB
Undecanone-(2)HMDB
2-UndecanoneChEBI
Chemical FormulaC11H22O
Average Molecular Weight170.2918
Monoisotopic Molecular Weight170.167065326
IUPAC Nameundecan-2-one
Traditional Nameundecan-2-one
CAS Registry Number112-12-9
SMILES
CCCCCCCCCC(C)=O
InChI Identifier
InChI=1S/C11H22O/c1-3-4-5-6-7-8-9-10-11(2)12/h3-10H2,1-2H3
InChI KeyKYWIYKKSMDLRDC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentKetones
Alternative Parents
Substituents
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point15 °CNot Available
Boiling Point231.00 to 232.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility19.71 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.09Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP4.25ALOGPS
logP3.92ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)19.64ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity53.03 m³·mol⁻¹ChemAxon
Polarizability22.66 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+143.72231661259
DarkChem[M-H]-140.72131661259
DeepCCS[M+H]+149.93630932474
DeepCCS[M-H]-146.70430932474
DeepCCS[M-2H]-184.05730932474
DeepCCS[M+Na]+159.14530932474
AllCCS[M+H]+145.632859911
AllCCS[M+H-H2O]+141.732859911
AllCCS[M+NH4]+149.232859911
AllCCS[M+Na]+150.232859911
AllCCS[M-H]-147.232859911
AllCCS[M+Na-2H]-149.032859911
AllCCS[M+HCOO]-151.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-UndecanoneCCCCCCCCCC(C)=O1593.3Standard polar33892256
2-UndecanoneCCCCCCCCCC(C)=O1271.1Standard non polar33892256
2-UndecanoneCCCCCCCCCC(C)=O1292.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Undecanone,1TMS,isomer #1CCCCCCCCC=C(C)O[Si](C)(C)C1475.9Semi standard non polar33892256
2-Undecanone,1TMS,isomer #1CCCCCCCCC=C(C)O[Si](C)(C)C1442.0Standard non polar33892256
2-Undecanone,1TMS,isomer #2C=C(CCCCCCCCC)O[Si](C)(C)C1439.5Semi standard non polar33892256
2-Undecanone,1TMS,isomer #2C=C(CCCCCCCCC)O[Si](C)(C)C1446.8Standard non polar33892256
2-Undecanone,1TBDMS,isomer #1CCCCCCCCC=C(C)O[Si](C)(C)C(C)(C)C1697.3Semi standard non polar33892256
2-Undecanone,1TBDMS,isomer #1CCCCCCCCC=C(C)O[Si](C)(C)C(C)(C)C1623.6Standard non polar33892256
2-Undecanone,1TBDMS,isomer #2C=C(CCCCCCCCC)O[Si](C)(C)C(C)(C)C1653.8Semi standard non polar33892256
2-Undecanone,1TBDMS,isomer #2C=C(CCCCCCCCC)O[Si](C)(C)C(C)(C)C1628.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2-Undecanone EI-B (Non-derivatized)splash10-0a4l-9000000000-0b50ecd5a4e139569f952017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Undecanone EI-B (Non-derivatized)splash10-0a4l-9000000000-0b50ecd5a4e139569f952018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Undecanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-52e32fb9de1c96bff48b2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Undecanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Undecanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4l-9000000000-3a214702b6cbf60221e02015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Undecanone Orbitrap 0V, positive-QTOFsplash10-00di-1900000000-89906bfdb8fd15dc3e5c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Undecanone Orbitrap 1V, positive-QTOFsplash10-00di-4900000000-6cfac7427fb901f030312020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Undecanone Orbitrap 1V, positive-QTOFsplash10-00dj-9700000000-930ae54f023a5d43c2de2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Undecanone Orbitrap 2V, positive-QTOFsplash10-007k-9400000000-36183b22a3eed18d676e2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Undecanone Orbitrap 3V, positive-QTOFsplash10-00l2-9100000000-682f78089ca57bf67bb92020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Undecanone Orbitrap 4V, positive-QTOFsplash10-067j-9000000000-0d844bdca90f6040bcd22020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Undecanone Orbitrap 5V, positive-QTOFsplash10-066r-9000000000-2420c6c12132e66e4f552020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Undecanone Orbitrap 5V, positive-QTOFsplash10-0aor-9000000000-a88e63ec19747439bb4f2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Undecanone Orbitrap 8V, positive-QTOFsplash10-0aor-9000000000-c6580cc292258ef555cc2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Undecanone n/a 11V, positive-QTOFsplash10-0002-9100000000-6513e75c4f7025c63fa12020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Undecanone n/a 11V, positive-QTOFsplash10-0a4i-9000000000-6069b457c0c038edb8df2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Undecanone n/a 11V, positive-QTOFsplash10-0aor-9000000000-f9fafeb5ba834b1e67102020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Undecanone n/a 11V, positive-QTOFsplash10-014i-9000000000-8470bd80251b1364df742020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Undecanone 10V, Positive-QTOFsplash10-0fk9-0900000000-8fcf8019b6b437d7957c2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Undecanone 20V, Positive-QTOFsplash10-0uk9-5900000000-c6f21e9a0d45a2555d702016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Undecanone 40V, Positive-QTOFsplash10-052f-9100000000-3a81d8fd09c96d9c283e2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Undecanone 10V, Negative-QTOFsplash10-014i-0900000000-8eaba4a1b4a0226760782016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Undecanone 20V, Negative-QTOFsplash10-014i-2900000000-4bd3f9e6cbf9a7cee0682016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Undecanone 40V, Negative-QTOFsplash10-0a4i-9300000000-ec90bdc81ba971e090582016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Undecanone 10V, Positive-QTOFsplash10-0aw9-9100000000-8b0a41317dc17902cd072021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Undecanone 20V, Positive-QTOFsplash10-0a4l-9000000000-05525b2199b1f5c37c4a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Undecanone 40V, Positive-QTOFsplash10-052f-9000000000-158a95c23b467002f89b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Undecanone 10V, Negative-QTOFsplash10-014i-0900000000-7a5d95d357c6f78b7dc12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Undecanone 20V, Negative-QTOFsplash10-014i-0900000000-9bafc5b07fd79d7c71312021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Undecanone 40V, Negative-QTOFsplash10-0006-9000000000-e98fa3a724a5700aeeea2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0-841.693 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected and Quantified0-11059.448 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothUlcerative colitis details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Crohn's disease
  1. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Ulcerative colitis
  1. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Associated OMIM IDs
DrugBank IDDB08688
Phenol Explorer Compound IDNot Available
FooDB IDFDB011831
KNApSAcK IDC00030758
Chemspider ID7871
KEGG Compound IDC01875
BioCyc ID2-UNDECANONE
BiGG IDNot Available
Wikipedia Link2-Undecanone
METLIN IDNot Available
PubChem Compound8163
PDB IDNot Available
ChEBI ID17700
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1021151
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .